Patent GB-784052-A (GB)
Title: Modification of the properties of synthetic fibres
Inventor: BAIRD WILLIAM
IPC: D06M13/432
Filed: 1954-02-12
Abstract: The tendency of synthetic fibres to accumulate static electricity is reduced by treating the fibres with a solution of a polymeric acrylic or methacrylic quaternary ammonium compound the monomeric form of which has the general formula <FORM:0784052/IV (b)/1> wherein R is hydrogen or methyl, R1 is an alkylene radical in which the carbon chain may be interrupted by hetero-atoms, N(tert.) is a group of atoms forming an aliphatic or heterocyclic tertiary amine, and X is a monovalent anion.  The polymer may be prepared either by quaternizing the monomeric ester and then polymerizing the product or by polymerizing the monomer and then quaternizing the polymeric product. The fibres are treated with the compound in aqueous or organic liquid solution at normal or elevated temperature, and after removal from the bath are generally dried at 50-150 DEG  C.  The anti-static effect so obtained is enhanced by subsequent after-treatment in a solution of soap or other anionic or non-ionic surface-active compound.  Examples are given.  Specification 784,051, [Group IV (a)], and German Specification 800,409 are referred to.ALSO:Polymeric acrylic or methacrylic quaternary ammonium compounds, the monomeric form of which have the general formula: CH2 = C(R)-COO-R1-N(tert.)X wherein R is hydrogen or methyl, R1 is an alkylene radical in which the carbon chain may be interrupted by hetero-atoms, N(tert.) is a group of atoms forming an aliphatic or heterocyclic tertiary amine, and X is a monovalent anion, may be prepared either by quaternizing the monomeric ester and then polymerizing the product, or by polymerizing the monomer and then quaternizing the polymeric product, the polymerization process in either case being carried out in the usual manner, using potassium or ammonium persulphate, sodium hydrosulphite or benzoyl peroxide as catalyst.  The quaternization may be performed by reacting the amino-ester with alkyl halides, aralkyl halides, alkyl sulphates or halogen substituted fatty acid salts.  Examples of suitable tertiary amino-alkyl esters from which compounds of the above formula may be prepared are dimethyl aminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, piperidino - N - ethyl methacrylate, hexamethyleneimino - N - ethyl methacrylate and morpholino - N - ethyl methacrylate.  Compounds in which the anion is a fatty acid residue, such as stearate, may be prepared from a quaternary compound containing another anion, such as halide, by metathesis with the sodium salt of the fatty acid. Specification 784,051 and German Specification 800,409 are referred to.ALSO:Acrylic or methacrylic quaternary ammonium compounds of the formula CH2=C(R)-COO-R1-N (tert.) X wherein R is hydrogen or methyl, R1 is an alkylene radical in which the carbon chain may be interrupted by hetero-atoms, N(tert) is a group of atoms forming an aliphatic or heterocyclic tertiary amine, and X is a monovalent anion, are prepared by reacting the corresponding acrylic or methacrylic amino-esters with alkyl halides, aralkyl halides, alkyl sulphates or halogen-substituted fatty acid salts.  Examples of tertiary amino-alkyl esters which may be treated are dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, piperidino-N-ethyl methacrylate, hexamethyleneimino-N-ethyl methacrylate and morpholino-N-ethyl methacrylate.  The quaternary compounds can also be made by interacting a halo-alkyl acrylate or methacrylate with a tertiary base, and the quaternation with pyridine of 4-chlorobutyl methacrylate (from methacrylyl chloride and tetrahydrofuran), 5-chloroamyl methacrylate (from methacrylyl chloride and tetrahydropyran), and the methacrylate of triethylene glycol chlorohydrin (from triethylene glycol chlorohydrin and methacrylic acid), is described.  Compounds in which the anion is a fatty acid residue, such as stearate, may be prepared from a compound containing another anion, such as halide, by metathesis with the sodium salt of the fatty acid. Specification 784,051 and German Specification 800,409 are are referred to.